I'm concerned about the impact that filing a claim would have on my insurance score and premiums for this property and other rentals.

Im not otherwise concerned about it breaking since I have other ways to heat the home. also A/C is only a few years old.

But the terms will tell you the answers - yes you can refinance but there may be a prepayment penalty That would be the least of my concerns.

Can everyone post what they know and where they are at as far as correspondences and solutions are concerned?

I'm constrained to being on title so completely understand that I'm accountable to the lending debt - not concerned about that.  

Your real estate agent can convey your concerns to the sellers' agent.

As far as saturation goes when the boom was hitting we started seeing regular homes and even mobile homes get converted to “cabin/chalet” rentals.  

I suspect the new title examiner has found something in the chain of title or the execution and notarization of your deed that makes them unwilling to rely on it to issue your buyer a policy without exception for the concern(s). 

Yeah, that was my concern is having a VA aimlessly make phone calls and not convert because they aren't asking the right questions.

However, always budget for unexpected issues, especially when adding square footage.Seller financing could indeed allow you to offer more, but you're right to be concerned about funding the rehab.